Dichloromethane → 2-Chloro-N-methoxy-N-methylnicotinamide

[Step 1] 5.0 g of 2-chloronicotinic acid and 2.8 mL of thionyl chloride were dissolved in 60 mL of benzene and then refluxed while heating. Three hours later, after adding the reaction liquid to 50 mL of a separately prepared dichloromethane solution containing 4.6 g of N,O-dimethylhydroxyamine hydrochloride and 20 mL of pyridine while cooling with ice, the solution was stirred overnight at room temperature. Following completion of the reaction, the solution was concentrated under reduced pressure, and the resulting residue was purified by recrystallization (with a mixture of ethyl acetate and hexane) to obtain 5.1 g of 2-chloro-N-methoxy-N-methylnicotinamide in the form of pale yellow crystals (79%).

1. temperaturerefluxed
2. temperaturewhile heating
3. additionThree hours later, after adding
4. temperaturewhile cooling with ice
5. customcompletion of the reaction
6. concentrationthe solution was concentrated under reduced pressure
7. customthe resulting residue was purified by recrystallization (
8. additionwith a mixture of ethyl acetate and hexane)

ORD record

ord-8fda6573713d4ea3853ac2dc14cfb939

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604030B2